Structural studies of dithiatetrazocines: X-ray crystal structures of the symmetric dithiatetrazocines p-XC6H4CN4S2CC6H4X [X = NO2, Br] and the first unsymmetric dithiatetrazocine, p-BrC6H4CN4S2CC6H4NO2

Bond, Andrew D.; Haynes, Delia A.; Rawson, Jeremy M.

doi:10.1139/v02-159

Cited by 15 publications

(14 citation statements)

References 18 publications

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“…Compound 1 , 2 , and 3 were synthesized respectively by Boeré et al, Gronowitz et al , and Bond et al The yields of compound 1 , 2 , and 3 were 5.4% , 5.0% , and 2.4% , respectively, because of air‐sensitive intermediate, 4‐aryl‐1,2,3,5‐dithiadiazolium chloride. 4‐Aryl‐1,2,3,5‐dithiadiazolium chloride would decompose when it exposed to air.…”

Section: Resultsmentioning

confidence: 99%

“…Based on quantum chemistry calculations, geometries of 3,7‐diaryl‐1,5,2,4,6,8‐dithiotetrazocine were optimized . The calculation results show that these compounds are planar.…”

Section: Introductionmentioning

confidence: 99%

“…However, the synthetic methods of 3,7‐diaryl‐1,5,2,4,6,8‐dithiotetrazocine in literatures were complex . Moreover, the yields of these compounds were very low.…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, developing an efficiently synthetic procedure would be very important to acquire the practical electron acceptor materials. In this paper, an one‐pot procedure that tri(trimethylsilyl)arylamidine reacted with SCl 2 to directly synthesize title compounds is reported to improve the yields from 2.4%–9.0% in literatures to 5.1%–29.3%.…”

Section: Introductionmentioning

confidence: 99%

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Syntheses and Optoelectronic Properties of Planar Compounds 3,7‐diaryl‐1,5,2,4,6,8‐dithiotetrazocine

Zhang

Shen

Yang

et al. 2015

Journal of Heterocyclic Chem

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Planar molecules 3,7‐diaryl‐1,5,2,4,6,8‐dithiotetrazocines would be potential acceptor materials of organic solar cell because of their containing SN units. One‐pot synthetic procedures of 3,7‐diaryl‐1,5,2,4,6,8‐dithiotetrazocine compounds are developed to improve their yields up to 2.1–5.9 times as much as those in literatures. The geometries of title compounds were optimized by the density functional theory calculations. Their optoelectronic properties were studied by ultraviolet and cyclic voltammetry spectra and fluorescence quenching experiments. The highest occupied and lowest unoccupied molecular orbital energy level values show that these compounds are suitable to be employed as acceptor materials for developing bulk heterojunction organic solar cells with high open circuit voltages. Emission fluorescence of poly(3‐hexylthiophene) at excited state in dichloromethane was quenched by addition of title compound. Therefore, these compounds used as acceptor materials could exhibit good mobility.

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Section: Resultsmentioning

confidence: 99%

“…Based on quantum chemistry calculations, geometries of 3,7‐diaryl‐1,5,2,4,6,8‐dithiotetrazocine were optimized . The calculation results show that these compounds are planar.…”

Section: Introductionmentioning

confidence: 99%

“…However, the synthetic methods of 3,7‐diaryl‐1,5,2,4,6,8‐dithiotetrazocine in literatures were complex . Moreover, the yields of these compounds were very low.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Syntheses and Optoelectronic Properties of Planar Compounds 3,7‐diaryl‐1,5,2,4,6,8‐dithiotetrazocine

Zhang

Shen

Yang

et al. 2015

Journal of Heterocyclic Chem

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“…[17][18][19][20][21] In regards to the latter, we recently reported the synthesis and detailed study of the optoelectronic and solid-state properties of thienylfunctionalized DTTA (1a) and its hexylated analogue 1b. [17][18][19][20][21] In regards to the latter, we recently reported the synthesis and detailed study of the optoelectronic and solid-state properties of thienylfunctionalized DTTA (1a) and its hexylated analogue 1b.…”

Section: Introductionmentioning

confidence: 99%

Influence of substitution pattern and enhanced π-conjugation on a family of thiophene functionalized 1,5-dithia-2,4,6,8-tetrazocines

2015

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Sulfur–Nitrogen Compounds

Chivers

2005

Encyclopedia of Inorganic Chemistry

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The quintessential sulfur–nitrogen compound, tetrasulfur tetranitride, S 4 N 4 , was first detected in 1835, just 10 years after the discovery of benzene. Its unusual structure, like that of benzene, was not elucidated for over 100 years. The application of diffraction techniques revealed the unusual cage arrangement with two weak cross‐ring sulfur–sulfur interactions. The details of the electronic structure of this fascinating molecule are still a matter for debate today. The polymer, (SN) x , was first obtained in 1910 and its metallic character was noted. However, it was the discovery in 1973 that a polymer comprising only nonmetallic elements behaves as a superconductor at 0.26 K that sparked widespread interest in sulfur–nitrogen (SN) chemistry. A year later it was proposed that planar SN heterocycles belong to a class of ‘ electron‐rich aromatics ’ that conform to the well‐known Hückel (4n + 2)π‐electron rule of organic chemistry. This suggestion, which was based on simple electron‐counting concepts, provided an additional impetus for both experimental and theoretical investigations of SN systems. In the past thirty years, the combination of structural studies, primarily through X‐ray crystallography, spectroscopic information, and molecular orbital calculations has provided reasonable rationalizations of the structure–reactivity relationships of these fascinating compounds. Interfaces with other areas of chemistry, for example, materials chemistry, organic synthesis, coordination chemistry, and biochemistry have been established and are under active investigation. For example, in the area of solid‐state chemistry, materials with unique magnetic and conducting properties that depend on intermolecular sulfur–nitrogen interactions between radical species have been designed. These new materials have potential applications in the construction of organic data recording devices. At the other end of the chemical spectrum, S ‐nitrosothiols (RSNO) have been shown to be important species in the storage and transport of nitric oxide. As NO donors, these SN compounds have potential medical applications in the treatment of blood circulation problems. This contribution begins with a short discussion of structure and bonding in cyclic SN species. This is followed by an overview of the various physical methods that are used to characterize SN compounds. The subsequent sections deal with specific classes of SN compounds starting with binary species, which include cations and anions as well as neutral molecules. The next sections are concerned with two important classes of reagents, SN halides and SN oxides. Heterocyclothiazenes, in which a sulfur atom in an SN ring is replaced by another atom, most commonly carbon, phosphorus, or a transition metal, constitute a continually expanding area of investigation as reflected in the relatively large section on this topic. Sulfanuric ring systems, which involve sulfur in the +VI oxidation state, have been known for many years and recent interest has revolved around polymers involving the NS(O)R repeating unit, which are isoelectronic with the well‐known polyphosphazenes. The next section describes the chemistry of cyclic sulfur imides, that are structurally related to the cyclic sulfur allotropes by the replacement of one or more sulfur atoms by an imido (NR) group. In the final sections, the unusual properties of SN chains, including the unique polymer (SN) x are discussed.

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Structural studies of dithiatetrazocines: X-ray crystal structures of the symmetric dithiatetrazocines p-XC₆H₄CN₄S₂CC₆H₄X [X = NO₂, Br] and the first unsymmetric dithiatetrazocine, p-BrC₆H₄CN₄S₂CC₆H₄NO₂

Cited by 15 publications

References 18 publications

Syntheses and Optoelectronic Properties of Planar Compounds 3,7‐diaryl‐1,5,2,4,6,8‐dithiotetrazocine

Syntheses and Optoelectronic Properties of Planar Compounds 3,7‐diaryl‐1,5,2,4,6,8‐dithiotetrazocine

Influence of substitution pattern and enhanced π-conjugation on a family of thiophene functionalized 1,5-dithia-2,4,6,8-tetrazocines

Sulfur–Nitrogen Compounds

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